HCID 20183020, compound → HCID 178445974, compound

HRID 255619Notes

Reaction equation

HRID 255619 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:37]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@@H:38]([OH:44])[CH2:39][C:40]([NH:42][NH2:43])=[O:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:49]([CH2:57][CH2:58][CH2:59][C:60](O)=[O:61])(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.ON1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]([NH:26][C@H:27]([C:34]([NH:36][C@@H:37]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@@H:38]([OH:44])[CH2:39][C:40]([NH:42][NH:43][C:60](=[O:61])[CH2:59][CH2:58][CH2:57][C:49](=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:41])=[O:35])[CH2:28][C:29]1[N:33]=[CH:32][NH:31][CH:30]=1)=[O:25])[CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 20183020HCID 20183020, compoundHCID 178445973HCID 178445973, compound

Product 1

HCID 178445974HCID 178445974, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

66 mg (0.1 mmole) of 4(S)-[N-benzyloxycarbonyl-3-(1-naphthyl)-L-alanyl-L-histidyl]amino-3(S)-hydroxy-6-methylheptanoic acid hydrazide (prepared as described in Example 5) were dissolved in 3 ml of dimethylformamide, and then 31 mg (0.1 mmole) of N-hydroxysuccinimide 4-benzoylbutyrate were added and the mixture was stirred for 2 days at room temperature. The resulting reaction mixture was concentrated by evaporation under reduced pressure, and water was added to the resulting residue. After the water had been added to the residue, the precipitate was separated by filtration. It was washed with water, and the powder obtained after drying was washed with ethyl acetate, to give 63 mg of the title compound as a white powdery solid melting at 158°-160°, [α]27 -44.4° (C=0.5, methanol).

Workup

  1. customThe resulting reaction mixture
  2. concentrationwas concentrated by evaporation under reduced pressure, and water
  3. additionwas added to the resulting residue
  4. additionAfter the water had been added to the residue
  5. customthe precipitate was separated by filtration
  6. washIt was washed with water
  7. customthe powder obtained
  8. customafter drying
  9. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-1989704b51b74dc6b8040bb340dea39b
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

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